Methyl iodide → 1-Methyl-2-(3-pyridyl)indole

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Reaction Steps

Under argon, a dimethylformamide (30 ml) solution of 2-(3-pyridyl)indole (3.07 g) was added to dimethylformamide (20 ml) in which 60% sodium hydride (0.76 g) was suspended and the mixture was stirred at room temperature for 30 minutes. Methyl iodide (1.2 ml) was added at 0° C. and the mixture was stirred at room temperature for one hour. The mixture was reacted at 0° C., then a saturated aqueous sodium hydrogencarbonate solution was added and the mixture was extracted with ethyl acetate. The organic phase was washed with brine and dried over magnesium sulfate, then the solvent was evaporated in vacuo and the residue was purified by silica gel column chromatography to obtain 1-methyl-2-(3-pyridyl)indole (1.72 g).

Provenance & Evidence